Base Camp

I joined AppDirect as Vice President of Engineering at the beginning of June. Friday was my 28th day on the job. The experience so far has been a whirlwind—there’s so much to do at a scaling startup. My calendar was literally already double-booked my first day on the job!

I knew the AppDirect opportunity was going to be challenging—but also extremely rewarding. As soon as I decided to join the team, I started preparing for the adventure.

True North: Seek empirical truth

Before I started my role at AppDirect, I did my research on both the company and the industry. I poured over the information on the corporate website to learn how the company positioned itself. I spoke with a company in Sydney to hear about competition in the space. I read articles in the tech press covering AppDirect’s fundraising and milestones. And I connected with former employees to gain insight about the team.

I learned that AppDirect was the leader in a category that Gartner defines as cloud service brokerage—connecting buyers and sellers of cloud services in a marketplace. But an easier way to describe AppDirect is this: it’s like Shopify, but for SaaS.

I discovered that although there were competitors, AppDirect secured a foothold in the industry and climbed faster than others in the category. Well-known brands like AT&T, Comcast Business, Deutsche Telekom, Softbank, and Telstra were customers. There were other companies on the same path, but AppDirect was in the lead and was nimbler in its ascent.

I read about the investment from J.P. Morgan which set the company’s valuation at $1B. AppDirect is the best kept secret in the industry: it’s a unicorn that most haven’t heard of. But some of the smartest investors on the planet recognize the potential of the company; Bessemer Venture Partners and Salesforce Ventures selected AppDirect for inclusion on the Forbes “Cloud 100” in 2016 (and again in 2017). The “Cloud 100” are the hottest private companies in cloud computing. AppDirect is listed alongside 99 stellar companies, including: Adyen, Dropbox, Slack, and Stripe.

Sometimes a change in direction is needed when scaling a team. This is why I joined.

Humility: Listen before being heard

As one of the newest members of the team, I’m keenly aware of how much I don’t know about the company’s situation. The AppDirect journey began years ago. To get to this point, the team has endured a steep, uphill climb. They know the obstacles that have been overcome and the detours that had to be taken. I’m fortunate to have been teleported to this point in the company’s ascent—I won’t take it for granted.

During my initial days on the job, I recognized my most important task was ramping up as quickly as possible. I needed to learn the values and culture of the company, the challenges facing the team, and the history of what has been attempted before. I also realized that I wouldn’t have all the answers. On the contrary, the team has the institutional knowledge and context to chart the best path forward.

Humility describes how David Marquet led sailors when he was in charge of U.S. Navy nuclear submarines. Now retired, Marquet wrote about his success in challenging the Navy’s traditional command-and-control leadership style. Instead of barking out orders to be carried out, he set the vision and the rationale for his crew—then allowed them to choose the specific methods by which to achieve the goals. Setting clear direction but leveraging the input of the team is a way to build a lasting, self-sustaining organization.

Setting clear direction but leveraging the input of the team is a way to build a lasting, self-sustaining organization.

My experience in the early days of Salesforce left me with memories of what it was like to scale one of the first SaaS companies. My time at Twitter left an imprint of how an Engineering team could decompose a monolithic code base and overcome technical debt. And my tenure at BigCommerce provided relevant understanding of what it takes to build a commerce platform. But each of these situations was unique, and the lessons of the past won’t translate exactly to the current situation at AppDirect.

I will rely on the team to help navigate our way to the next plateau.

Intensity: Invest the energy

Building a startup into a lasting company is a marathon—though it may consist of mini sprints along the way. It’s crucial for anyone leading the charge at a startup to have both the strength required for the climb as well as the stamina to complete the journey.

AppDirect has a globally distributed team, with Engineering primarily in San Francisco, Montréal, Buenos Aires, and Pune. Before I joined the company, I embraced the requirement to travel to other offices. During my 2nd week on the job, I visited our Montréal offices where I introduced myself to the company at our monthly Global Town Hall. My tenure is still less than 30 days, but as I write this I am at the airport for my 2nd trip to Montréal.

Others within the company are doing the same. Our co-CEO Nicolas Desmarais prompted me to visit Montréal and joined me on my first trip (along with our VP of Product, Michael Cassin). Teammates from across the globe regularly made the trek to our San Francisco HQ; I’ve already met face-to-face with colleagues from: Buenos Aires, Calgary, Montréal, Ottawa, and Pune. We’re constantly communicating across offices (and timezones) via email, Slack conversations, or Google Hangouts. This is what it takes to continue to grow our globally distributed business—and every person does their part.

But it’s also important to find balance between work and life, wherever you can find it. During my third week on the job, our Executive Leadership team held an all-day offsite to discuss strategy, company culture, and new initiatives. We were also joined by an external facilitator—Prakash Raman, who also leads executive coaching at LinkedIn. Prakash led a session by asking us to share each of our professional and personal goals. I think every person cited their desire to have a more effective balance between work and family time.

This struggle is common among many in the startup world. In a recent blog post, VC Mark Suster described his need to set more boundaries by lamenting “I only have 7 trips left” with family.

I’ll do my best to expend the necessary energy required for the climb, but (just like my colleagues) I’ll constantly strive to maintain balance outside of work.

Overcoming difficult obstacles can be even more challenging with a bad or defeatist attitude. The last thing you need in a startup is an individual who is negative in their outlook, as this can spread to other members of the team.

Startups are hard. There will be tough times. Colleagues at all levels make mistakes — including among the leadership ranks. I’ve made mistakes at prior companies: I’ve made snap judgments without full information, and communicated things that I later realized had to be re-stated. No situation (and no person) is perfect. What matters most is how an individual — and how the team — responds to mistakes and adversity.

In an op-ed piece in the New York Times, legendary climber Alex Honnold attributed his success to this: “…if I have a particular gift, it’s a mental one—the ability to keep it together where others might freak out.” Honnold’s positive mental attitude prevents the mountain from owning him—he owns the situation and the outcome.

During an all-hands meeting in Montréal, I asked the team to bring their Positive Mental Attitude to work each and every day. We’re in the trenches together, and when one person is dejected or discouraged, it helps if they are surrounded by colleagues with a resilient attitude. It can make all the difference for team health and stability.I’ll do my best to lead by example.

Ownership: Take full responsibility

A final key ingredient in a successful startup is for every employee to have an ownership mindset. This is easiest to achieve during the early days, when the team is relatively small and it’s literally possible to know everyone in the company. I’ve seen this first-hand at early stage startups: trust is shared, communication is straightforward, and everyone understands how each role contributes to the company. In these early days, people wear multiple hats and there is little to no “specialization” of roles.

As a startup reaches scale, it becomes harder to have that cohesion across departments and offices. What was once a small, intimate group of colleagues starts to feel like a disconnected large company. It becomes harder to communicate across large groups of people in different departments—a challenge that becomes more pronounced with offices across cultures and time zones. It becomes easy for team members to lose that ownership mentality. I’ve been part of a company that was once a scrappy upstart (where everyone felt the burden of ownership) and watched it evolve into a large corporation (where ownership was gradually diminished across the team).

This is one of the biggest challenges in growing a company: achieving scale and specialization of disciplines while maintaining the trust, alignment and ownership of a small startup. I firmly believe that constant communication within and across departments is the best way to maintain the ownership mindset—if you don’t know what’s happening in the business, how can you feel like an owner? I’m focusing a large percent of my energy on communicating up, down, and across the company.

Another facet of ownership is this: not accepting the role of victim. Every person in a startup has the power and the responsibility to improve the situation. If there’s a challenge to be overcome, don’t “admire the problem”—do something about it! That’s the attitude that motivates entrepreneurs to start companies, and it’s the same attitude that should run rampant among employees of a thriving startup.

Values-Based Leadership

During my interview process, I first learned about the values of the company: